Diary of a Leader: In Operational Leadership You Can’t Improve What You Don’t Understand
- Lindsay Sheldrake
- Nov 2
- 4 min read
Welcome to Diary of a Leader: Real Stories, Leadership Lessons, and Personal Growth
Ah, leadership. It asks us to make things better — to refine, improve, and move forward. But sometimes, in our urgency to fix, we skip the one step that matters most: understanding.
Because improvement without understanding isn’t progress — it’s assumption disguised as action.
Welcome back to Diary of a Leader, a behind-the-scenes look at what it takes to build alignment, trust, and operational rhythm inside growing businesses.
If you’ve ever launched a new process that looked good in theory but fell apart in reality, this one might feel familiar.
The Story: When Process Becomes Presumption
Last week, I caught up a previous colleague — someone sharp, capable, and deeply grounded in process. She works as a procurement contract specialist inside a large organization.
Her world is built on precision: contracts, compliance, supply chains, and approvals. Every action triggers another, and each small handoff has ripple effects. In this kind of environment, “we’ll figure it out later” isn’t a strategy — it’s a liability.
But lately, she’s been frustrated.
After a few questions (and a laugh about being “paper pushers”), we uncovered what was really happening. Her department had a new director — brought in, as she put it, “to make things more efficient.”
At first, that sounded positive. Efficiency matters. Productivity matters.
But what followed was a leadership misstep I’ve seen too many times.
The new director wanted to improve how the team worked — faster approvals, fewer bottlenecks, better flow. But instead of starting with discovery, he jumped straight to design.
When he announced his new process, the team did exactly what you’d hope from a group of engaged professionals. They offered insight. They volunteered to walk him through how things really worked — the checks, the dependencies, the hidden steps that don’t show up on the org chart.
And his response?
“Thanks for the offer — I know what I’m doing.”
The Domino Effect
The new process looked great in theory.
It just didn’t work in practice.
Key checkpoints were removed, approvals were condensed, and the double-verification step that protected the business from compliance risk was quietly deleted. Within weeks, errors began creeping into supplier agreements. What seemed like small misses snowballed into larger issues that threatened timelines, budgets, and relationships.
The irony? The department was now slower and more frustrated than before.
And the people who cared most — the ones who’d offered to help — were disengaging. My friend and her manager (the layer between her and the director) had already started updating their résumés.
What failed wasn’t just a workflow.
It was trust.
What It Taught Me About Operational Leadership
You can’t improve what you don’t understand.
Every organization has a “current state” — the real way work moves through the business. Not the ideal, not the documented version, but the lived reality of how things actually happen.
Skipping that understanding is like building on sand. The structure might look solid for a while, but it’s unstable underneath.
Leaders often skip discovery because they feel pressure to act. They equate speed with progress. But the most effective leaders know that observation is action. Listening is strategy. Understanding is momentum — because it anchors every decision in truth.
When leaders involve the people closest to the work, they don’t just gain information. They gain credibility. They build buy-in. And they uncover the nuances that no dashboard or spreadsheet can reveal.
The Ripple Effect of Skipping Discovery
When leaders design in isolation, they create systems that look perfect on paper — and impossible in reality.
Processes start to fail quietly: a missed approval here, a duplication there. Teams start improvising, building side systems to fill the gaps. And before long, the “efficiency initiative” becomes another layer of work.
The bigger cost, though, is cultural.
When people offer input and are ignored, they stop offering it. When they stop offering it, the organization stops learning.
Change done to people rarely sticks.
Change done with people builds resilience, adaptability, and ownership.
The Leadership Lesson: Progress Requires Partnership
Before you can design a better system, you have to understand the one that already exists.
That’s what discovery really is — partnership. It’s an act of respect. It tells your team, I see you, I value your insight, and I trust your perspective.
Leadership isn’t about being the expert in every system. It’s about being the connector — the one who listens across functions and translates complexity into clarity.
When we do that, we don’t just build better processes.
We build better relationships.
And that’s what sustains operational excellence.
Reflection Prompts for Leaders
Where might I be improving without first understanding?
Have I mapped how work actually flows — not how I assume it does?
Am I making space for my team’s experience to inform the design of change?
Wrapping Up: Change Without Understanding Isn’t Progress
This conversation reminded me that leadership isn’t about knowing more — it’s about seeing more.
Real improvement doesn’t come from moving faster. It comes from moving smarter — with clarity, evidence, and shared understanding.
Because you can’t improve what you don’t understand.
And you can’t lead what you refuse to learn.
Want support designing systems that scale — without losing alignment?
Book a Discovery Call to explore how we can uncover your current state and build clarity that actually sticks.
Stay tuned for more real-world lessons on leadership, operational clarity, and purposeful growth in the next installment of Diary of a Leader. Because leading teams and managing projects isn’t about doing it all. It’s about focusing on what matters most—and doing it with intention, rhythm, and excellence.
